Benzocaine → benzoic acid, 4-[(phenylsulfonyl)amino]-, ethyl ester

HRID 1068864Notes

Reaction equation

HRID 1068864 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([S:19]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 262295benzoic acid, 4-[(phenylsulfonyl)amino]-, ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g (30.3 mmol) of ethyl 4-aminobenzoate were dissolved in 100 ml of pyridine and admixed dropwise at 0° C. with 4.1 ml (31.8 mmol) of benzenesulfonyl chloride. The mixture was stirred for 3 h. The mixture was then concentrated under reduced pressure and the residue was recrystallized from ethanol. 7.3 g (85%) of the product were obtained.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5e698fd4d7844c84a91fd07c27d1b3a8
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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